There’s excitement weaving between the happenings of First Friday Art Walk.

By Sarah Moore

No need to despair the passing of summer, September is a time to rejoice in the bearable temperatures, the russet and gold-tinged landscapes, and the parking spaces and bar stools suddenly freed up by the mass exodus of all the tourists. First Friday Artwalk may be at its peak in summertime in terms of sheer numbers, but it’s fall when the monthly extravaganza truly comes into its own. That back-to-school mentality abounds creativity among the community, so plan your Friday night out around art and aperitifs.

Before you dive into the action on Congress Street, you’re going to need some liquid fortification. Working under the theory that you should start and end your night with the best drinks, we head to Rhum (pictured following page bottom left, 4 Free Street, 536-1774, rhumportland.com). Style is cyclical, and tiki bars appear to be back in. Rhum adopts the theme with a hearty dose of tongue-in-cheek: think cocktail umbrellas, leis, and even a banana made to look like a dolphin garnishing your rum drink. Thankfully, it’s saved from going full Hawaiian shirt-style by the subterranean, nightclubby feel of the space. We take a seat at the expansive rectangular bar beneath the palm grass thatch and order a couple of Jungle Birds ($12), a potent mix of Black Strap rum, Campari, pineapple, and cherry bitters that taste like the last sips of summer.

Continuing with the kitsch theme, we round the corner to Pinecone & Chickadee, part gallery, part gift shop (pictured bottom right, 6 Free Street, 772-9280, pineconeandchickadee.com). You probably didn’t even realize you needed a DIY Terrarium kit with ornate brass plant mister until you came in here. Owners Noah DeFilippis and Amy Teh expanded the space back in February to showcase monthly exhibitions by local artists and illustrators. The atmosphere is akin to a lively house party hosted in your quirky friend’s living room, complete with beer, wine, and finger food.

“We’re a store, so we approach things differently. You can buy the art straight off the walls,” says curator Kris Johnson. The October Artwalk will open with “The Ghoul School 2,” an homage to 1980s horror flicks and teen sub-culture by illustrator Ryan Lamunyon. We grab a can of Bissell Brothers from the ice box and gather around the eye-catching exhibition wall at the rear of the building. This is a place where art feels fun, local, and accessible.

Into the Action

Moving into the heart of the festivities, Monument Square teems with performers and artists. It’s almost impossible to weave through the throngs without becoming distracted by an elaborately dressed belly dancer or steel drum troupe. Unable to resist the pull of the window dressing, we drop into the Maine College of Art(522 Congress Street, 775-3052, meca.edu). MECA periodically hosts exhibitions by students and faculty members, as well as showing visiting artists. The ICA Gallery on the ground floor will open in October with a new exhibition entitled “In this Realm,” featuring paintings by five Maine artists exploring the themes of gender and identity. Alas, no refreshments of the alcoholic variety here, which is little surprising given the number of thirsty underage art students milling about. Luckily, immediately next door, SPACE Gallery (538 Congress Street, 828-5600, space538.org) boasts a bar. The drink selection may not be extensive (we keep it classy and grab a couple of Miller High Lifes), but the eclectic roster of music, art, and film nights that the community-run gallery hosts nightly certainly make up for it.

“October Art Walk will open with the inaugural New England Art Book Fair,” says Event Programmer Adam Stockman. “It’s something SPACE has wanted to do for a long time.” More than 45 vendors will pack out the small space to sell everything from zines to art tomes, the perfect draw for collectors or those who simply want to decorate their coffee table.

After crawling our way up the main drag–filled with so many artisan vendors it looks like Etsy exploded onto Congress Street–we find ourselves in need of refreshments. Taco Escobar (548 Congress, 541-9097, tacoescobarr.com) is packed shoulder to shoulder with a young and buzzing crowd of locals and visitors alike, jostling for space under the strings of multicolored lights and pulsing pop music. Once there, we order the delicious Toasted Coconut Margarita ($9) along with some Chipotle Sweet Potato Taquitos ($7) to balance the heedless mixing of drinks.

The saying goes, ‘All roads lead to Rome.’ In the same way, all art walks lead to the Portland Museum of Art (7 Congress Square, 775-6148, portlandmuseum.org). Free to the public from 4 p.m.-8 p.m. every Friday evening, the expansive gallery has embraced the fall school-days feeling with not one, but three exhibitions based around books and literature. The star show of the October Art Walk will feature a collection of books and illustrations by pioneering French artist Henri Matisse, including copies and prints of the artist’s iconic 1947 book, Jazz. While there, you can’t fail to miss the 13- x 34-foot canvas by artist Tim Rollins and the Kids of Survival charity, which will adorn the wall of the Selma Black Great Hall. Entitled A Midsummer Night’s Dream, the installation is inspired by the roguish Puck of Shakespeare’s riotous comedy. Head downstairs to the PMA Workshop for an interactive art experience. Channel your inner Rockwell Kent by illustrating your own interpretationof Herman Melville’s Moby Dick. A speciality cocktail from Aurora Provisions in the PMA café is sure to fuel your creativity.

Longfellow bound

The PMA can feel like the last stop in the artwalk path, with High Street acting as a natural boundary to the action. However, there’s more to be explored if you wend your way up towards Longfellow Square. If you’re footsore from traversing the many corridors and corners of the PMA, the diminutive but inviting She Bear Gallery (pictured opposite page top left, 650 Congress Street, 239-2088, shebeargallery.com) is a welcome alternative. “We’re off the beaten path a bit,” says owner Jenny Smick, who opened She Bear in 2013 to showcase the charming woodblock prints by her late mother, Holly Mead. She Bear will also be showing a visiting exhibition of unusual acrylic narrative paintings by Massachusetts artist Steve NegrÓn, opening on the night of the October Artwalk. “It’s not your typical Maine art in here,” says Smick. “We don’t feature seascapes and lighthouses. I prefer things a little more…eclectic.”

The same can be said of Nathaniel Meiklejohn, owner the Bearded Lady’s Jewelbox (pictured opposite page top right, 644 Congress Street, 747-5384, thebeardedladysjewelbox.com). Hard to find but rewarding to discover, the bar certainly feels like the inside of an antique jewelry case, with mismatched antique glassware, tiny bouquets of wildflowers, and a whimsical mural of the eponymous bearded ladies dominating the wall to the right of the curving pine bar. Tucked away upstairs in the mezzanine, an Aladdin’s Cave of antique furniture and potted plants, we sample the O.D.B. cocktail–rye whiskey, dry vermouth, Campari, and fresh grapefruit juice. This is the spot to while away the evening, sipping on delicious and potent cocktails in the bohemian enclave until the darkness deepens and it’s time to go home. n